US 12,325,722 B2
Process for the preparation of high purity norbornene silyl ethers
Hugh Burgoon, Akron, OH (US); J. Alex Niemiec, Akron, OH (US); Doug Skilskyj, Akron, OH (US); and Larry F. Rhodes, Akron, OH (US)
Assigned to PROMERUS, LLC, Akron, OH (US)
Filed by PROMERUS, LLC, Akron, OH (US)
Filed on Mar. 15, 2024, as Appl. No. 18/605,925.
Claims priority of provisional application 63/452,364, filed on Mar. 15, 2023.
Prior Publication US 2024/0309025 A1, Sep. 19, 2024
Int. Cl. C07F 7/18 (2006.01)
CPC C07F 7/188 (2013.01) 12 Claims
 
1. A process for the preparation of a compound of formula (I):

OG Complex Work Unit Chemistry
wherein
n is an integer from 1 to 10, inclusive, and where one or more of CH2 is optionally substituted with (C1-C10)alkyl or (C1-C10) perfluoroalkyl;
m is an integer from 0 to 2, inclusive;
R1, R2 and R3 are the same or different and independently of each other selected from the group consisting of hydrogen, halogen, methyl, ethyl, linear or branched (C3-C12)alkyl, (C3-C12)cycloalkyl, (C6-C12) bicycloalkyl, (C7-C14)tricycloalkyl, (C6-C10) aryl, (C6-C10) aryl(C1-C3)alkyl, (C5-C10) heteroaryl, (C5-C10) heteroaryl(C1-C3)alkyl, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12) bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10) aryloxy (C1-C3)alkyl, (C5-C10) heteroaryloxy (C1-C3)alkyl, (C6-C10) aryloxy, (C5-C10) heteroaryloxy and (C1-C6) acyloxy;
R4, R5 and R6 are the same or different and independently of each other selected from the group consisting of methyl, ethyl or linear or branched (C3-C12)alkyl and substituted or unsubstituted (C6-C14) aryl;
comprising:
placing a solution of tris(pentafluorophenyl) borane in a suitable reactor under inert atmosphere;
adding to the above solution a mixture of a compound of formula (II):

OG Complex Work Unit Chemistry
and a silane of formula (III):
R4R5R6SiH  (III)
over a period of 10 minutes to 120 minutes at a temperature from 25° C. to 80° C.;
allowing the reaction mixture to react for an additional period of 15 minutes to 120 minutes;
cooling the reaction mixture to room temperature and treating with a suitable base selected from the group consisting of lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonium hydroxide, tetramethyl ammonium hydroxide and pyridine; and
distilling the reaction mixture under vacuum at a temperature of from 130° C. to 170° C. to obtain the compound of formula (I); and wherein the amount of tris(pentafluorophenyl) borane employed is less than or equal to 0.2 mole percent based on moles of the compound of formula (II) employed.